Trifluoroiodomethane → HCID 14154578, compound

HRID 1904092Notes

Reaction equation

HRID 1904092 reaction equation
[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[C:10](I)[CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4].[F:16][C:17](I)([F:19])[F:18]>[Cu].N1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[C:14]2[C:9](=[C:10]([C:17]([F:19])([F:18])[F:16])[CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)=[O:4]

Participants

5

Reactant 2

HCID 16843TrifluoroiodomethaneHCID 57214028HCID 57214028, compound

Product 1

HCID 14154578HCID 14154578, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 1049PyridineSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5-iodo-1-naphthalenecarboxylic acid methyl ester [8.8 g, 28 mmoles, described by C. Seer and R. School, Justus Leibigs Ann. Chem., 398, 82 (1913)], trifluoromethyl iodide (12 g, 61.2 mmoles) freshly prepared copper powder (5.7 g, prepared according to the procedure of R. Q. Brewster and T. Groening, "Organic Syntheses", Coll. Vol. II, John Wiley and Sons, New York, N.Y., U.S.A., 1948, p. 445) and pyridine (45 ml) was charged into a stainless steel autoclave. The vessel was shaken and heated at 130° C. for 24 hr and cooled to room temperature. The mixture was filtered to remove insoluble material. The filtrate was washed with 1 N aqueous HCl, water and brine, dried (MgSO4) and concentrated to dryness. The residue was crystallized from methanol to give 4.3 g of 5-(trifluoromethyl)-1-naphthalenecarboxylic acid methyl ester, NMR (CDCl3) δ4.0 (s, 3H), 8.0 (m, 6H).

Workup

  1. customprepared
  2. temperaturecooled to room temperature
  3. filtrationThe mixture was filtered
  4. customto remove insoluble material
  5. washThe filtrate was washed with 1 N aqueous HCl, water and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated to dryness
  8. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-041afd6ab7834537b945ca7a35de9c08
Source dataset
uspto-grants-1984_03
Patent number
US04439617

Reaction notes

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